Shoes and watches...are key.
Hey I get compliments on my shoes on regular basis...
No white shoes or running sneakers, thats a big no-no, maybe ok for High school.
I agree to get some some 'casual hip bowling shoes' (less than $100) I agree with going with something from Diesel Wish, Kenneth Cole Reaction, or even something like a Timberland Lexington. Cole Haan more like $130. Don't worry about paying too much, but get 2-3 pairs to rotate them, 2 black and 1 brown is good. Even some of those skechers are ok, but they are a bit cheaper.
Pair that with some nice faded jeans (kenneth cole, DKNY, Seven, etc), good $50-100 belt, a nice fitted T-shirt (no logos, $25-50) and the nicest watch you can afford (I sport a Breitling). You will be money.
If you have the cash, invest in nice pair of black dress shoes ~300ish (allen edmonds, ferragamo, gucci, etc). Don't get cheap with these, as you will have them for years...
Invest in good quality stuff, better to buy one $75 belt than 4 $15 belts. Even if you get one piece at a time, remember Quality over quantity.